D-glutamic acid γ-p-nitroanilide | 60133-17-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: D-glutamic acid γ-p-nitroanilide
• 英文别名: γ-L-glutamyl-5-(p-nitroanilide)；D-γ-glutamyl para-nitroanilide；D-γ-glutamine-p-nitroanilide；D-γ-glutamyl-p-nitroanilide；D-γ-Glu-pNA；D-GpNA；H-D-Glu(pNA)-OH；(2R)-2-amino-5-(4-nitroanilino)-5-oxopentanoic acid
• CAS: 60133-17-7
• 化学式: C₁₁H₁₃N₃O₅
• mdl: MFCD00063693
• 分子量: 267.241
• InChiKey: WMZTYIRRBCGARG-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-glutamic acid γ-p-nitroanilide 在 γ-glutamyl transpeptidase 水 作用下， 生成 4-硝基苯胺
  参考文献：
  名称：

  大鼠肾脏γ-谷氨酰转肽酶的稳态前动力学研究证实了其乒乓机制†

  摘要：

  γ-谷氨酰转肽酶（GGT）参与细胞排毒，白三烯的生物合成和控制谷胱甘肽的生理浓度。它还在帕金森氏病，糖尿病，细胞凋亡抑制和癌症耐药性中起重要作用。它催化体内分解底物谷胱甘肽，通过裂解γ-谷氨酰基和半胱氨酰甘氨酸部分之间的酰胺键。苏氨酸被认为在酰化步骤期间在γ-谷氨酰酰基酶中间产物的形成中充当GGT的亲核试剂。然后，将γ-谷氨酰基部分转移至伯胺受体底物（氨基酸或二肽）或水分子上，以分别在转酰胺基化或水解反应中形成含有新的异肽键或谷氨酸的化合物。尽管GGT在人类生理学中的作用很重要，但缺乏有关其催化反应机理的信息，尤其是在酰化步骤中形成的中间体的性质方面缺乏信息。为了深入了解酰基酶中间体的形成，请使用不同的D在对位上被吸电子基团和给电子基团取代的-γ-谷氨酰苯胺在水用作受体底物的条件下用作供体底物。对于脱氢是限速步骤的稳态水解反应，获得了斜率为零的哈米特图。为了确认乒乓机制，然后使用供体底物D

  DOI：

  10.1002/poc.777

文献信息

• Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and Their kinetic studies with γ-Glutamyltranspeptidase
  作者：Christian Lherbet、Mylène Morin、Roselyne Castonguay、Jeffrey W Keillor

  DOI：10.1016/s0960-894x(03)00083-0

  日期：2003.3

  A new series Of L-glutamic acid p-nitroanilide analogues has been synthesized and tested as substrates and inhibitors of rat kidney gamma-glutamyltranspeptidase (GGT). Kinetic parameters (K-m and k(cat)) were determined for each analogue and provide insight into the scope and limits of GGT catalytic efficiency. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A small chimerically bifunctional monomeric protein: Tapes japonica lysozyme
  作者：K. Takeshita、Y. Hashimoto、T. Ueda、T. Imoto

  DOI：10.1007/s00018-003-3082-z

  日期：2003.9.1

  The lysozyme of the marine bilave Tapes japonica (13.8 kDa) is a novel protein. The protein has 46% homology with the destabilase from medicinal leech that has isopeptidase activity. Based on these data, we confirmed hydrolysis activity of T japonica lysozyme against three substrates: L-gamma-Glu-pNA, D-gamma-Glu-pNA, and epsilon-(gamma-Glu)-L-Lys. The optimal pH of chitinase and isopeptidase activity was 5.0 and 7.0, respectively. The isopeptidase activity was inhibited with serine protease inhibitor, but the lytic and chitinase activities were not. Moreover, only isopeptidase activity is decreased by lyophilization, but lytic and chitinase activities were not. We conclude that T. japonica lysozyme expresses isopeptidase and chitinase activity at different active sites.
• ——
  作者：L. Ghizdavu、C. Bălan、L. David、C. Bâtiu、O. Cozar、D. Ristoiu

  DOI：10.1023/a:1012029626570

  日期：——

  New complexes CuL2. 2H(2)O, CoL2. 3H(2)O, MnL2. 2H(2)O and FeL3. 2H(2)O, L=gamma -L-glutamyl-5-(p-nitroanilide), were synthesized and characterized by their spectral, magnetic and thermal properties. The thermal stabilities of the synthesized complexes were examined in the temperature range 20-500 degreesC. In all these complexes gamma -L-glutamyl-5-(p-nitroanilide) acts as a bidentate ligand, its coordination involving the carbonyl oxygen and the nitrogen atom of the second amino group. The local structure around the Cu(II) ion is pseudotetrahedral. In the Co(II), Mn(II) and Fe(III) complexes, the metal ions are in the high-spin form, with octahedral stereochemistry.
• Pre-steady-state kinetic studies of rat kidneyγ-glutamyl transpeptidase confirm its ping-pong mechanism
  作者：Jeffrey W. Keillor、Annie Ménard、Roselyne Castonguay、Christian Lherbet、Caroline Rivard

  DOI：10.1002/poc.777

  日期：2004.6

  of GGT in the formation of the γ-glutamyl acyl enzyme intermediate during the acylation step. The γ-glutamyl moiety is then transferred to a primary amine acceptor substrate (an amino acid or dipeptide) or to a water molecule, to form a compound containing a new isopeptide bond or glutamate in the transamidation or hydrolysis reactions, respectively. In spite of the importance of the role of GGT in human

  γ-谷氨酰转肽酶（GGT）参与细胞排毒，白三烯的生物合成和控制谷胱甘肽的生理浓度。它还在帕金森氏病，糖尿病，细胞凋亡抑制和癌症耐药性中起重要作用。它催化体内分解底物谷胱甘肽，通过裂解γ-谷氨酰基和半胱氨酰甘氨酸部分之间的酰胺键。苏氨酸被认为在酰化步骤期间在γ-谷氨酰酰基酶中间产物的形成中充当GGT的亲核试剂。然后，将γ-谷氨酰基部分转移至伯胺受体底物（氨基酸或二肽）或水分子上，以分别在转酰胺基化或水解反应中形成含有新的异肽键或谷氨酸的化合物。尽管GGT在人类生理学中的作用很重要，但缺乏有关其催化反应机理的信息，尤其是在酰化步骤中形成的中间体的性质方面缺乏信息。为了深入了解酰基酶中间体的形成，请使用不同的D在对位上被吸电子基团和给电子基团取代的-γ-谷氨酰苯胺在水用作受体底物的条件下用作供体底物。对于脱氢是限速步骤的稳态水解反应，获得了斜率为零的哈米特图。为了确认乒乓机制，然后使用供体底物D